Million Dollar Musings: MLB DFS Picks Today for Monday 5/5

by Dave Potts (CheeseIsGood) Last Updated 2025-05-05 16:13:19 Premium Content Part of the product MLB DFS

Whether you are looking for the top pitchers or the best stacks, Dave Potts (aka CheeseIsGood) has you covered with an extensive deep dive into his MLB DFS picks. Cheese, one of the preeminent baseball minds in all of fantasy sports and a winner of a $1,000,000 1st-place prize on both DraftKings and FanDuel, is here to give you his musings on the upcoming MLB DFS slate.

Happy Monday! We kick off the week with an 8-game slate that has the potential to turn into a 7-game slate with a straight Orange rating on the MLB weather for the SDP/NYY game. For now, I’m keeping that game in the analysis, but personally, I don’t plan to have much exposure to it unless things clear up significantly throughout the day.

We also need to note that while both sites have an 8-game slate, they are slightly different slates at slightly different start times. DK is starting at the usual 7:05 p.m. ET, while FD is starting early at 6:40 p.m. ET and then cutting off the 2 later games. I’ll include all the games in the analysis; just be aware that some of these plays are not available on both sites.

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Monday Pitching: MLB DFS Picks on FanDuel & DraftKings

We have a tough slate on both sides tonight. The weather in the SDP/NYY game adds to the already tricky nature of this slate, along with at least some moderate question marks surrounding the clear SP1.

TOP TIER PITCHING

• Cole Ragans vs. White Sox – 35.9% K, 7% BB, 4.40 ERA, 2.40 SIERA
• Nick Pivetta at Yankees – 29.3% K, 6% BB, 1.78 ERA, 3.04 SIERA
• Carlos Rodon vs. Padres – 31.7% K, 11.6% BB, 3.43 ERA, 3.33 SIERA
• Brady Singer at Braves – 26.7% K, 8.9% BB, 3.24 ERA, 3.57 SIERA
• Bryce Miller at A’s (DK) – 24% K, 14.7% BB, 3.52 ERA, 4.65 SIERA
• Matthew Boyd vs. Giants – 20.7% K, 9% BB, 2.70 ERA, 4.29 SIERA
• Luis Severino vs. Mariners (DK) – 18.1% K, 7.1% BB, 3.30 ERA, 4.28 SIERA
• Landen Roupp at Cubs – 25.9% K, 10.4% BB, 5.10 ERA, 3.74 SIERA

OK folks, this is going to be a weird mess right out of the gate. The mess is exacerbated by the weather in New York, which may well take Pivetta and Rodon out of the mix. Even if that game were no issue, at first glance, Cole Ragans looks like the wildly obvious must-play SP1. Using long-term stats, even just 2025 stats and matchups figured in, it might even appear to be a good old Don’t Overthink It. I am kind of still leaning towards that being the case, but there are some very obvious issues here. I bet most of you remember the last time Ragans was a Don’t Overthink It just a couple of weeks ago when he was pulled after 3 bad innings at home against Colorado. He had a disturbing drop in velocity during that start, and it turns out that he was dealing with a mild left groin strain, which caused him to miss his last start. Of course, it’s great that it was not an arm injury, but it’s now been 17 days since his last healthy start, so of course there is still some possibility that he is not at full strength. At the very least, I’d say his risk of a shorter outing is higher than normal. But if we assume he’s fine, then he is in a tier of his own on this slate and the very clear top play in all formats on all sites.

Because we have such a clear gap between Ragans and everyone else, my lean here is to play him and know that even if something goes wrong, he’s so highly owned that you can probably survive it. But I will also say that if I had no concern at all, I might well play 100% Ragans, and I am absolutely not going to do that here. I need to look at this next group of options before I decide how and where to fade this potentially great chalk, then we’ll loop back.

Both Nick Pivetta and Carlos Rodon have Ragans-like ceilings when things go right for them. Both of them have been up around the 30% strikeout range this season, with Rodon striking out 7+ batters in 6 of his 7 starts, while Pivetta has 9+ strikeouts in 2 of his last 4 starts. The ceiling can match Ragans’s, but the matchup is a clear downgrade for both. For Rodon, the downgrade comes from the lack of strikeouts in the San Diego lineup, while with Pivetta, the downgrade comes from the power risk in the Yankees lineup. Now we add in the weather risk, and I just don’t see how I can play these guys ahead of Ragans. If we get the all-clear, I will have them both in the MME pool, with a slight preference for Pivetta.

Bryce Miller survived some wonky control in his last start, and we learned later that he was dealing with a sore back, which is probably why he was pulled after 5 innings. However, the wonky control can’t just be blamed on the back, as he now has multiple walks in every single start this season. The strikeouts have also been more up and down, and while I believe in the talent here, this guy just doesn’t look like a trustworthy ace at this moment. The salary looks about right at $8,100, and the matchup does not give him any additional boost. With every passing moment, it’s getting harder to justify a Ragans fade.

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